When taking long trips, traveling in a vehicle early in the morning, or driving late at night, vehicle passengers may wish to sleep in the vehicle while traveling. Often times, passengers cannot find a comfortable and supportive position for sleeping in a vehicle while seated and restrained by seatbelts. Neck pillows can be bulky and are only useful if a passenger remembers to bring them along before a trip. Thus, a headrest assembly with an integrated and selectively deployable head support enhancement feature is desired.